R. Sultanov, R. R. Ismagilov, N. R. Popod’ko
Nov 15, 2013
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0
Influential Citations
11
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Journal
Journal of Organometallic Chemistry
Abstract
Abstract The stereoselective carbomagnesiation reaction of bicyclo[2.2.1]hept-2-ene, endo -tricyclo[5.2.1.0 2,6 ]deca-3,8-diene, and exo – endo -5-methylbicyclo[2.1.1]hept-2-ene with EtMgX, where X = Cl or Et, occurs in the presence of catalytic amounts of TaCl 5 to give chloro- and ethyl[2- exo -(2′-norbornylethyl)]magnesiums in high yields. The multistep reaction mechanism involving norbornene and ethylene through tantalacyclopentanes as key intermediates is also postulated. DFT calculations confirm the thermodynamic preference for the resulting exo product.